I Interviewed Hundreds of Elite CEOs About the Top 20 Secrets to Success and Lost Touch with My Identity

Beleaguered, I plopped down in another cold leather desk chair across from yet another elite CEO. My journey to interview hundreds of elite CEOs and write a blog article about the top 20 secrets to leadership success had taken me to five states, 15 cities and countless offices across the US and this 58th day of interviewing didn’t feel any different. But that’s when everything changed. 

Perhaps I should back up a few steps and give you some context. Several months ago, I was sitting at my desk as a copywriter in Austin when I noticed that everyone around me was succeeding. What could I be doing wrong that everyone else was doing right? Why had I been created this way? Determined to succeed, I set out on a mission: ask a bunch of successful people what I should be doing. 

That’s enough context, right? No? Okay, let’s back up again. It’s my senior year at Columbia. In just a few short weeks, I’ll set off as an intern at a big banking firm down the street. I’m over the moon with anticipation. I had never been so happy in my life. I could tell that I was on the brink of something great. That’s the day I met my darling wife. 

Okay, so back to the present time. Earlier that day, I was getting coffee with my first elite CEO of the day and she was telling me the usual story when I started to get deja vu. The story she was telling me and the advice she was passing my way felt so familiar. Like I had known it all along! 

After the meeting, I called my friend Sam to see if he was in town. Sam and I did our undergrad years at Harvard together. He went on to work for his father’s production company in LA, while I stayed behind in Boston to help run my family’s real estate hedge fund. Two family boys! Sam and I had a quick chat on the phone about how business is doing and agreed to meet at the steakhouse later. 

I headed off to my next interview with an elite CEO, not knowing it would be the last interview of my journey. He sat me down and told me the usual story when I looked down at one of the pictures on his desk, and noticed a familiar face. There I was, staring right back at myself. I couldn’t believe it! Did he print this photo and frame it before our interview? Did my darling wife and kids send it to him as a prank? Looking up from the photo, I started to wonder why this person was in my office. “Get out of my office!” I yelled across the room. I called my assistant and had security escort this man off the premises. 

With only a half hour left until the board meeting, I had a lot to prepare in a small amount of time. I guess you could say that’s my sweet spot: high stress, high pace. Life’s pretty good at the top.